My knowledge of hats doesn’t extend much beyond a bashed-up straw boater in the summer. As such I tend to panic on receiving an invitation to a fancy-schmancy event that involves wearing a headpiece. I have the feeling I’m not alone – our generation tends to our muddle through when it comes to hats, against a backdrop of tutting from our mothers and grandmothers. But given ’tis the season of weddings, regattas and races (Ascot takes place 20-24 June), I decided to seek expert advice on the subject. Hats off (sorry!) to Sarah Main, owner of Hats Whiskers boutique, near Faringdon, Oxon, where you can buy or hire headpieces. Here are her top tips for finding The One…

The trilby, oversized bows and sculptural fascinators – all by the Hats Whiskers

Try on loads

When it comes to buying a hat, it’s a case of trial and error, so try on every colour, shape and style you can get your hands on to find the one that best frames your face. Be open-minded and allow yourself plenty of time – it’s not a purchase you can rush. Either choose your hat first and then build your outfit around in – for instance, you might fall for a wild, jazzy hat so then you’ll need a reasonably plain dress. Or if you’ve got your outfit already sorted, take it in store, put it on (we have changing facilities in the shop) and find the hat that works best with it.

Think about the variables

Face shape, skin tone and your hair should all be taken into account. If you have a small face, for example, a big hat can make you look like a mushroom. Or if you have pale olive skin, a yellow hat might not reflect very well onto your face. Black works for most, although some people can wear heavier fabrics than others. And think about how you’ll style your hair on the day and ensure your hat works with it. Get someone to take some photos so you can see how it looks from all angles.

Don’t fear the fascinator

Fascinators sometimes get a bad rap but they come in all shapes and sizes, and sometimes it’s hard to tell where a large fascinator becomes a hat (see the fierce fascinators on Kate Middleton and Anna Friel above). My advice is to not worry about all of that and don’t dismiss fascinators out of hand – again, just try on a selection of styles and you might be surprised.

On the big day

Allow yourself plenty of time to fix the hat in place without accidentally stabbing yourself with the hat pin – it’s a good idea to practise beforehand. There’s nothing worse than rushing and than bashing the top of your hat on the car as you jump in. Check the back view and side angles in the mirror – have you positioned it correctly?

Confidence is key

Once you’ve committed to your hat, wear it like you mean business! Try not to be nervous because it will show in your posture, demeanour and expression. Don’t constantly fiddle with it and move it around. With the right hat you should be able to put it on, hold your head up high and forget about it.